Synthesis of deoxyfrenolicin and nanaomycin A

Abstract

Deoxyfrenolicin and nanaomycin A have been synthesized. Key steps in the synthesis include a phthalide annulation reaction to produce a naphthoquinone, a tandem Diels-Alder/retro-Claisen reaction to produce the carbon skeleton, and a stereoselective reduction of a hemiketal.